4,4-Diethoxy-1-phenyl-but-2-yn-1-ol → 4,4-Diethoxy-1-phenylbut-2-yn-1-one

HRID 1952586Notes

Reaction equation

HRID 1952586 reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[C:5]#[C:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])[CH3:2]>ClCCl.O=[Mn]=O>[CH2:16]([O:15][CH:4]([O:3][CH2:1][CH3:2])[C:5]#[C:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])[CH3:17]

Participants

4

Reactant 1

HCID 108898484,4-Diethoxy-1-phenyl-but-2-yn-1-ol

Product 1

HCID 127649924,4-Diethoxy-1-phenylbut-2-yn-1-oneYield 84%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

4,4-Diethoxy-1-phenyl-but-2-yn-1-ol (9.46 g, 40.38 mmol) was dissolved in dichloromethane (200 ml) and treated with activated MnO2 (100 g) at rt for 15 h. The reaction mixture was filtered through a plug of celite and Na2SO4. The filtrated was concentrated under reduced pressure to afford the desired ketone (7.85 g, 84% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite and Na2SO4
  2. concentrationThe filtrated was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4af9c38d92f44d03a06dff6f6e4eb45b
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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